Vice President of Sales

Vice President of Sales - New Logo

Department: Sales

Remote U.S. 

Position Overview

The VP Sales – New Logo will play a crucial role in driving Raintree’s growth strategy by leading and expanding the New Logo sales team. This high-impact, high-visibility role will be responsible for achieving significant revenue targets, optimizing sales processes, and building a high-performance sales organization. Reporting directly to the CRO, they will be a key member of the senior management team, contributing to strategic decision-making and business development initiatives.

Raintree is seeking a dynamic, proven executive to lead its New Logo Sales team and bring a wealth of knowledge and experience to implement best in class processes. The ideal candidate is analytically driven, a creative problem solver, and brings an entrepreneurial “roll up your sleeves player/coach” approach to their work. The VP Sales will lead Raintree’s New Logo team by setting priorities, increasing win rate, and expanding the business through bringing in new customers while demonstrating creativity, innovation, and initiative. They will be responsible for transforming the sales organization by reviewing and optimizing key systems and processes, including performance management and tracking, compensation structures, territory planning, and other critical operational functions.

A key responsibility will be to build a high-performing sales team with top-quartile performance, ensuring that the team not only meets but consistently exceeds sales objectives. The candidate will also be responsible for establishing and executing a robust sales strategy that positions the organization for sustained growth and success. There will be occasional travel (from 25% to 50% outside the candidate’s local market may be necessary).
 

Key Responsibilities

• Strategic Leadership:

  • Develop and execute a comprehensive sales strategy to drive growth in new logo sales.

  • Implement a segmented go-to-market strategy across small, medium, and large/enterprise prospects.

  • Continuously assess market trends, customer needs, and competitor moves to inform strategic decisions.

• Team Building and Management:

  • This role has supervisory responsibilities for a team of 8 new logo sales representatives.

  • Recruit, hire, develop, and mentor a high-performing sales team with a focus on achieving >$10M in Annual Recurring Revenue (ARR) from new logos.

  • Lead a team that consistently hits quota, with >75% of team members achieving their targets.

• Sales Execution:

  • Standardize the selling process and guidelines to increase the sales close rate.

  • Set quarterly and annual sales goals, design rep territory assignments, and put in place an outbound-oriented sales motion and performance-based sales culture.

  • Engage directly in key deals to provide senior management sponsorship and close critical opportunities.

• Metrics-Driven Management:

• Partner with Rev Ops to deliver accurate sales forecasts, budgets, and performance reports.

  • Utilize data and metrics to track team performance, coach reps, and drive accountability.

  • Implement rigorous KPIs and metrics to ensure disciplined execution and continuous improvement.

  • Collaborate cross-functionally, particularly with marketing and product deployments, to build a predictable go-to-market model and seamless customer experience.

Key Competencies & Experience Required

• Proven track record as a successful B2B SaaS sales leader with a healthcare IT/EHR background, leading teams responsible for new logo sales with a history of generating $10-15M in new logo bookings annually.

• Skilled in assessing existing sales teams and developing forward-looking organizational plans that swiftly manage out underperformers. Proven track record of hiring top-performing reps who consistently hit or exceed their quotas, with a history of engendering strong loyalty within the sales team—can provide examples of team members who have followed them from company to company.

• Demonstrated success in selling to customers across segments, including large enterprise customers (with an average selling price of ~$750K+/ACV and a 6–12 month sales cycle), as well as middle-market ($100k/ACV) and SMB ($5k/ACV) customers.

• Prior experience in designing and implementing predictable full lifecycle sales motions, including optimizing sales enablement processes, setting quotas and compensation, and segmenting customer targets thoughtfully.

• Expertise in designing, instituting best practices, and ensuring adherence to sales processes and systems (CRM, performance management, territory design, etc.). Experience with Salesforce CRM.

• Experience in healthcare SaaS and/or EHR that sells to the private post acute facilities and medical groups is highly desirable.

• Performance-driven management style, with a strong ability to use data to track team performance, coach reps to success, accurately forecast outcomes, and drive accountability across the team.

• A culture builder and strong people leader with demonstrated experience in managing complex organizations through periods of transformation and change.

• Experience in closing deals, including providing senior management sponsorship and stepping in to close key deals when necessary.

• Ability to lead a fully remote sales team located across the U.S.

• Demonstrated track record of collaborating with all members of an executive team to develop and refine a go-to-market approach, with a highly agile mindset.

Our Perks

Remote Work/Work From Home

Paid Time Off/11 Paid Holidays/Year-End Holiday Break

Health, Dental, Vision, HSA/FSA,

401K with Company Match

Disability & Life Insurance

Employee Assistance Program

Paid Parental Leave

About Raintree Systems​

Raintree is the preeminent platform for enterprise and mid-sized therapy provider organizations. Our award-winning solutions in patient engagement and communications, clinical documentation, revenue cycle management (RCM), and business intelligence are tailored to the needs of physical therapy, occupational therapy, speech therapy, and ABA practices across all treatment settings.

Our Core Values

We put our Clients First - We are Open and Honest - We are Disciplined, Yet Flexible

We love to Solve Problems - We are Committed to Greatness - We are a High Performance Team

Raintree Systems provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.